Succeeding on your own. Nate Kontny of Draft

Nate is the entrepreneur who succeeded on his own and here’s his story and the tools he’s using.

Since we’re the marketplace for startup tools, we’re keen on knowing the workflows of entrepreneurs we admire — we talk to them about the tools they’re using to do their jobs and how they’re using them. From these conversations the Workflows series was born: To inspire and empower entrepreneurs.

Nate is the entrepreneur who succeeded on his own, and writing is his thing.

He has been building Draft to help us become better writers: to get that first draft done, to experiment more with revising and editing, to build bigger audiences around our writing. This started from his own struggle with word processors, but, more importantly, his struggle at one of his previous startups, Inkling.

At the end of 2005, Nate co-founded Inkling and got accepted into Y Combinator. He remembers being frustrated about how little the news about his company was spreading. Back then, he always wanted somebody else to get the word out. He wanted to get more press and more blogs to write about his startup. “And it sucks to feel that way”, as he puts it.

Nevertheless, this didn’t stop Inkling from growing. When it had matured enough, Nate decided to begin a new project, Cityposh. It was a gaming platform and another Y Combinator company. Sadly (or not), it didn’t turn out as expected. It had to be shut down.

Now Nate is a solo founder who is getting the word out by himself. He admits that “At first, it felt awful having to do everything on my own, but, like most challenges, there’s usually an opportunity.”

The opportunity lays in how fast he can move and make decisions. He doesn’t have anyone else he needs to convince to do one thing or the other. And this ability to move quickly ends up being the most useful skill and tool a startup can have.

“So as other tools like Google Docs sit there with very few changes — you can imagine the bureaucracy probably needed to get a new idea into Google Docs — I can keep implementing new idea after new idea. Since Draft was released over a year ago, I’ve averaged about 3 major features every few weeks. People notice that kind of speed at which a product improves and appreciate the frequent effort of creators in making their lives a little bit better.”

Nate’s Kit

Here are the tools Nate is using to build Draft, spread the word about it, and keep things improving:

- Draft
- Intercom
- New Relic
- Outpost
- Stripe
- Mac Mail App
- Twitter
- Svbtle
- Github
- Sublime Text
- MailChimp
- Baremetrics
- WuFoo
- Mention
- Buffer
- Google News Alerts
- Clicky

Writing, Nate’s most important job as Draft’s founder

A product has no value without an audience — it needs actual people to enjoy it and make room for it in their workflows. That’s why Nate considers writing his main job: “Writing has been a super important skill, tool, thing that I do for Draft, for building my career, for building the next thing”. He writes on popular publications’ websites such as FastCompany and BetaBeat and, on his blog, Ninjas and Robots, hosted by Svbtle. Actually, he was one of the first people to be invited to publish on Svbtle.

By writing in all these different places, he builds his audience and, of course, he gets new customers for Draft. And that’s what every entrepreneur wants, right? But here’s what not every entrepreneur wants: to do the hard work and spend the time necessary to get there.

Nate has spent around 8 years blogging to become better as a writer and all this effort has clearly paid off. Now, he doesn’t need to email bloggers to try to get people to pay attention to him — all he needs to do is simply write to those thousands and thousands of people he gathered around him during the years.

There’s one important lesson he learned during this time spent building an audience: “learn how to tell a story”. This might sound very simple to some of you, yet it is extremely powerful. Also, the reality of doing it can be unexpectedly harsh.

To get to know how to tell a story, Nate thinks one should read some books on storytelling, learn about its principles, and how to put it in practice in different contexts. “While you’re learning how to tell a story, it becomes really apparent what’s missing from most people’s blogging and writing”. A hero.

They miss the fact that people want a hero, they want to root for somebody who goes through some sort of pain and struggle. People are trying to share their experience on blogs but they don’t think much about what makes those articles good stories. That’s what is missing from people’s writing, the struggle they’ve gone through to get at that specific point they’re talking about.

Let’s take one example. You see everywhere on the web articles like “Here’s how I got 2000 new Twitter followers”. That’s fine, but it’s boring because there’s no story there. The author misses that he could get much more interest into this piece if he shared some of the struggle it took him to learn this. “If you could tell me how hard it was for you to get your first project off the ground and why now it’s important to get new Twitter followers, now you have me wrapped in your story”.

Finding writing inspiration

Surprisingly, Google News Alerts is one of the tools Nate uses to get his writing inspiration — “It’s an underrated tool. I’ve just started using it more and I’m getting good at it”. He considers it a “secret weapon” to differentiate from the crowd as it helps him write about stuff one won’t find on popular tech sites such as Hacker News and Reddit. The thinking behind using Google News Alert as a differentiator is pretty simple: if you’re going to read only these popular sites you won’t find new ideas, you’ll just keep seeing the same things over and over again.

To not fall into this trap and find stuff he hasn’t seen before, he adds in Google News Alert words that describe the type of news he likes. For instance, Nate is a huge Malcolm Gladwell fan. He likes his books even though he doesn’t always agree with what Gladwell is saying. It’s just that Malcolm is “such a great storyteller” and his books are counter-intuitive. He’s making people think a little bit differently about the world. Given this, Nate has the word “counter-intuitive” as a search in Google News and he constantly gets emails letting him know what’s new all around the world on the topic. Of course, there’s a lot of junk in those emails. But sometimes they unveil real gems he’d have never found otherwise, like the story of a golfer named Jason Allred.

Nate used to play golf, but he doesn’t play too much now. He has never watched golf, never talked to somebody about golf. Yet an article about a golfer and a creative way he’s got into a tournament hits his inbox and then becomes the subject of one of his articles on BetaBeat. It showed up on one of his Google Alerts.

To write better, read more

Nate is an avid reader spending a great deal of time just using his Kindle. He wants more and more books to read because they fuel his writing: they either give him news ideas, or they become the subjects of his blog posts.

Because he keeps cycling through books so fast, he doesn’t like buying paper books anymore. Moreover, he loves electronic books. They accommodate very well his belief that people shouldn’t read books to completion when they don’t like them. Feeling the need to finish one because you’ve paid for it is a very common trap. “If you don’t like a book, move on. There’s so many beautiful writers and people with great ideas. If you get stuck on a book, why torturing yourself getting through it?”

To feed his pleasure of reading a lot of books, Nate subscribed to “Any new books”, a weekly newsletter he highly recommends. He gets by email all the new interesting books that are published on Amazon, categorised.

Draft — Nate’s Swiss army knife

Deeply knowing your core tool, the one that helps you do your most important job, is one great thing that gets you closer to success. Building yourself that core tool, well, that brings things to a whole new level. Just watch Nate. “Draft is kind of my Swiss army knife”. He constantly uses it for writing, customer support, image hosting (he sends links to Draft documents instead of image files), publishing his blog and tweets.

Draft is up all day long and there’s not a day that goes by that he doesn’t write something in it: his articles, any other text he produces, and even his to do list that also acts as a product roadmap.

After trying all the popular to do lists for iPhone and Mac, he realized that there are too many features that make people think more about their to do lists rather than actually do things. The solution he came to? The 1 minute to do list: he keeps track of 3 things he wants to accomplish the current day, 10 things he wants to accomplish soon, and then a list with other things he wants to do someday. He reviews what’s in ‘soon’ once a day, and once a week what he has been collecting in the ‘someday’ list.

When discovered, the 1 minute to do list felt like a revelation that made him wonder why he hadn’t been keeping a simple to do list like this before. It also became his product roadmap: “here are 3 things I wanna work on in Draft now, here are 10 things I might work on (bucket of things people have asked for and I want to maybe consider to do later on the road).” He doesn’t want to try to sketch out more than that because “Who knows how long these are gonna take?”.

While he doesn’t try to promise anything with roadmaps to his customers, he does support them when they have any issue with his tool. He sends them links to Draft documents where he adds screenshots and directions. He also cares about constantly improving. This is not about pushing new features but rather about improving the product, letting people know that he’s listening to them and their needs. As he always has good ideas coming from his audience, he wants to let his customers know that he’s constantly iterating on Draft. “It’s important to keep the cycle going”, so every three weeks, he tries to send a new email about the stuff that Draft has been improved, or fixed. His updates emails are now pretty famous and well appreciated.

Undoubtedly, Draft has become his thing.

Daily routine: writing and helping his audience

Nate is a man of routine who doesn’t like going to an office or to cafes to work. He loves working from home where he can control the noise volume and where he doesn’t have to have the radio on. Even though his routine was changed by their newborn and he’s still working on it, it will probably fall back to something similar to his previous one: checking out if Draft is ok and everything is healthy immediately after waking up, then quickly going through emails to see if there’s any major problem or issue, working on Draft, writing at least 250 words, and then working out from home following P90X program by Tony Horton.

He writes at least 250 words per day (but often it’s more than that) because he wants to publish at least one blog post every week and to also write articles for FastCompany, BetaBeat, or interviews with other publications. It’s a habit he has been building for years now.

When it comes to keeping in touch with his audience and to helping them, he uses several tools: Mail App for Mac, Intercom, WuFoo, Mailchimp, and Twitter.

Nate always tries to get back to people’s emails as fast as he can because the longer an email sits in his inbox, the less likely he will respond to it. “I don’t like to procrastinate on replying to something. If I can answer in a couple of minutes, I’ll do it”. He doesn’t use the Gmail web interface, but the Mail App for Mac which he really likes. That’s also because he has email accounts all over the place and he didn’t do the extra work of forwarding all of them to one email address. He doesn’t file emails because it’s an extra step, so he uses search if he needs to find something.

When talking about Intercom, Nate called it “kind of a Swiss army knife for messaging”. It is a very handy tool that he uses quite a bit these days for support, to let people know about what new features he released, to send out newsletters every few weeks, and to remind people that it would be great to support Draft monetarily.

But Intercom wasn’t that useful to Nate in the beginning. At first, he thought he would use it just to keep track of users and what they were doing. Down the road, it kept becoming more and more valuable. There was an AHA moment when he realized that he could encourage people to pay him money and a lot of them ended up doing so through that Intercom window. In fact, the messaging with Intercom could be considered a business model similar to Reddit Gold.

“There are millions of people that just use Reddit for free. But then there are enough people that buy something called Reddit Gold. It’s basically a little bit better version of Reddit. And that’s what I’m trying to do with Draft. Use Draft for free but if you want a little bit better version which doesn’t have any advertising, doesn’t bug you, you can just upgrade for just a little bit of money.”

On his blog, he encourages people to subscribe to his newsletter which he sends with Mailchimp. After subscribing, they get a WuFoo form to fill out some information about them — “WuFoo is a great online form creation tool that is really helpful when you got a new idea or a new contact form to create”.

Another channel he uses to get in touch with his audience is Twitter, where he’s got a lot of saved searches: for his blog address, his Twitter handle and links to Draft. Because the web version of it does a very decent job with saved searches and emails it sends out, he doesn’t use any other Twitter client. Sometimes, he does use Buffer to space out his tweets although he’s not the heaviest of their users. Even so, he recognizes it as helpful tool and that’s why Buffer was one of the first integrations he has put into Draft.

What’s important when choosing a tool

Nate tries to keep his tool use pretty basic and stick to those tools that he’s familiar with. For instance, Draft is built with Ruby on Rails, which he’s been using for 9 years. Sure, there are a lot of other new frameworks and tools he could use, but he likes to stick to those he’s familiar with because he gets really fast and good at using them.

He learned this from his father, who used to be a carpenter involved in constructions. As Nate grew up, his father had a tons of tools and did a lot of work around the house. What Nate remembers is how old his tools were — he wasn’t always buying new saws or new hammers but he kept using to his old tools he knew really well.

That’s a lesson most startups today don’t understand — they are constantly trying to use new tools and they’re slow in doing so because they simply don’t know how to use those tools. And they don’t take the time to get to master them.

When choosing his tools, Nate follows some criteria which he puts in these few words, “If you look at Draft, that’s the stuff I like”. So, he appreciates those tools that:

• are simple, have the fewest buttons and no distractions;
• have a workflow that feels light and easy to follow;
• let him get started really quick;
• save him time and steps in any process he’s doing every day.

Also, he doesn’t take signing up for something that costs money very lightly. He’ll test things, he’ll even pay to test things, but then he will cancel quickly if not satisfied. “I need more efficiency. I don’t need a new idea or a new tool that nobody has thought of. I basically need you to fix the stuff I’m already doing”. Also, if there are new good ideas, he’d like to see that the developer is still around fixing the tool and adding really good thinking to it. When this is not the case, he replaces the tool, as was the case with TextMate.

He used to use TextMate all the time and then it seemed like they stopped improving, when competitors like Sublime were continually improving — “there were really good ideas that were coming from Sublime and missed by TextMate”. So he switched to Sublime which “is just awesome right now and it’s kind of hard to tear me away to look for new tools. They’ve got a plug in system that works really well.”

The most important metrics: revenue, spreading of writing, and Draft’s performance

These three metrics are constantly monitored by Nate and they are those telling him how good he’s doing.

In terms of deciding whether Draft is on the right path or not, Nate only cares about revenue. He uses Stripe to process payments, and every day he checks his account there: “How much money did I make today? How much money did I make this month?”. He loves Stripe because it’s a really simple tool with great documentation and easy to integrate into any app. Over the years, he has used a lot of different payment processors — APIs and tools — and clearly Stripe is the best.

He doesn’t use any other tools to track Draft’s progress. He just looks at his Stripe dashboard asking “Am I improving this month versus last month?”. It’s true that he has signed up for Baremetrics (it provides Stripe analytics) which he finds to be a beautiful looking tool, well designed and well thought out, but he has troubles working it into his workflow. He hasn’t figured out yet what step Baremetrics is saving him “Right now, it’s an extra step for me.”

In regards to the outreach of his writing, the bigger his audience grows, the more he can spread the news about what Draft is doing. To track this, he’s monitoring his Twitter following “I don’t spend a great deal of time on this, but I do keep an eye on my followers count. Twitter is kinda the new RSS feed.” If his followers count is growing, he knows he’s doing a decent job encouraging people to follow what he’s writing. He’s also using analytics, but he pays little attention to that.

When it comes to Draft performance, he cares about how many people signed up the previous day, so he gets an email from Intercom. Of course, he doesn’t want this number to go down — he wants it to stay constant or to keep growing.

Then he cares about how fast Draft is, if it’s up and performing ok. He’s in New Relic all the time making sure Draft has a decent performance score. He has been using it since it started years and years ago. He’s also a big fan of Outpost which provide daily automated test and then send out emails with the status. If something goes wrong, they manually overlook.

One more tool that he uses to monitor stuff is Mention. If his name or something about Draft comes up, he gets an email to notify him. It’s kind of a Google News Alert for your stuff on social media platforms.

Advice for sole founders and entrepreneurs: learn to design, teach others, and be your own PR person

Nate strongly believes that entrepreneurs in general should find something that people are already doing and save them steps. That’s how they can be sure they’re building something valuable.

Then there are sole founders. One of their big problems is that they are too technical and they don’t do design. “They feel like they’re good software developers, but they suck at design”. So they think they need to hire someone to take care of this part. To these people he recommends a very good book: “Bootstrapping Design” by Jared Drysdale. It’s a quick read that goes through five or so important things to think about if you’re a developer trying to learn about design. It walks you through web typography, choosing colors, white space, and other really basic stuff that developers don’t really appreciate about aesthetic design. By the way, it has nothing to do with bootstrapping.

Also, technical sole founders should realise that even quickly going through a tutorial would open up their minds: “You know what? You could do this yourself. If you want to make an app, a website, and you’re really technical and you think you can handle the back-end but you’re feeling stuck because you don’t know how to design and you don’t have a designer as a co-founder, you could do this yourself.” Well, it might not be as pretty as all beautiful designs we see out there, but it’s possible for you to do it. You can get better at it and make something simple enough that people don’t hate using just by following some key principles.

To get started with design, there’s one framework which Nate’s a big fan of and he recommends to others: Twitter Bootstrap. His advice is to avoid using the defaults by tweaking it enough that it looks unique — pick unique colors and unique fonts. And that’s how you developers can stop sucking at design.

For people who aren’t good at marketing, Nate has also a solution: become a writer, work on your writing. It is possible to become a better writer and it’s going to take you a while, but it’s worth it. If you think you don’t have anything interesting to share, think again. Everybody has something to share.

“I don’t care how boring you think your life is. You went through something to get to this age of yours that was interesting. You had a challenge going through school, or growing up, or even learning how to play a sport or learning how to study. All of that is interesting to somebody who is younger than you, who hasn’t done this. You learned how to go through grade school. This is huge to someone who hasn’t gotten through grade school yet.”

If you think you need a PR, or a marketing person, or someone to be extroverted, become a teacher on your blog. You should teach others more because if you’re doing this consistently enough, it pays good results. You just have to keep doing it. If you practice getting good at it, in the end you’ll get there. And Nate is the best example you could have.

“I’m not extroverted. I don’t like going out. I’m an introvert. I like hanging in the back of the room. I don’t like going to conferences and talking to people. But because of my writing which is something I’ve been working on, I’ve been able to spread this thing to lots of different people.”

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This article was also published on The Underdog